Want to go to Hawaii in Summer of 2012. What points should I collect?

My wife and I would like to travel to Hawaii this summer for our anniversary. My question is this, what points should I collect over the next 10ish months so that we can fly and sleep in style (or at least cheap and fun) for Hawaii?

Details:
I've been collecting and using points since 2010. Between the two of us we have about 260,000 airline points in various programs (mainly AA and Continental). We don't really travel enough (2 trips this year) to do crazy things like mileage runs or gain any sort of status. We simply churn credit cards.

I'd look now for flights on AA that go through DFW in First Class to get to HNL or OGG. ORD-HNL is apparently seasonal now so you'd have to see if those dates work for you (stopping Jan 9, starting back up June 14). AA's first class on this route is similar to their international business class (missing IFE though) and I loved it when I flew it. These are popular routes so starting earlier is the best bet.

You can fly United from MKE-ORD-HNL for 20,000 saver award miles/passenger economy or 60,000 saver award miles/passenger first class. (Your Continental miles will automatically transfer to United next year.) To take advantage of the lower priced saver awards, you should book well in advance.

You can find a good hotel in Hawaii for 30,000 United award miles/night.

Consider opening a Chase Sapphire Preferred account to build miles quickly-- you can transfer them 1:1 to United Mileage Plus.

Between the two of us we have about 260,000 airline points in various programs (mainly AA and Continental).

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This is a point that needs to be addressed. I don't *think* you can merge points between spouses into a single account, and know you can't merge AA/CO. Thus, unless you have the required amount in a single account, it is going to make answering the question a little more difficult. Can you give us the number of points in each account to assist in answering?

This is a point that needs to be addressed. I don't *think* you can merge points between spouses into a single account, and know you can't merge AA/CO. Thus, unless you have the required amount in a single account, it is going to make answering the question a little more difficult. Can you give us the number of points in each account to assist in answering?

If you go after the Chase Sapphire Preferred card for that 50K bonus, you can transfer the points from two cards into one person's UA/CO or Hyatt account. But you're right, it doesn't do much for the existing miles. It's not clear how those are divided, but it might make sense to purchase separate award tickets.

You didn't mention how long you plan to stay in Hawaii, but I would say definitely get your flights now unless you don't have enough miles for two. Maybe also research on which island you'd like to visit - I have been to Maui and Big Island, both are very nice. Once you have your flights booked you can then work backwards and see how many points you still need for your ideal hotel stay. That way, you can focus on collecting points in the specific program.

You didn't mention how long you plan to stay in Hawaii, but I would say definitely get your flights now unless you don't have enough miles for two. Maybe also research on which island you'd like to visit - I have been to Maui and Big Island, both are very nice. Once you have your flights booked you can then work backwards and see how many points you still need for your ideal hotel stay. That way, you can focus on collecting points in the specific program.

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Agreed... if you have a truckload of AA miles left over after the flights, you can always head over to useaamiles.com and try to use miles and/or miles & cash to book the hotel and car.

definitely consider SPG and Hyatt. 5 nights at a decent SPG hotel in Hawaii ~48K points. Both of you can apply for the card now. If you can meet the spending, you would get ~50K Spg points total. SPG points can be transferred between family members.

I would go with Ultimate Reward points to start. You can get 50k with the Sapphire, and another 50k with the Ink Bold. These transfer 1 to 1, instantly, to Continental/United and to Hyatt. Since you reported having both AA and Continental miles built up, you might want to consider one way awards: fly there on United and back on AA (or vice versa). You can use the Ultimate Rewards points to supplement your Continental stash if necessary. Since the return flights (assuming you are US based) are usually overnight, make sure the return is on a flight with lay flat seats.

For lodging: the Grand Hyatt in Kauai is amazing. So if you can swing the Hyatt card (another Chase card), that will give you two nights, plus you can get additional nights using Ultimate Rewards transfers.

My wife and I would like to travel to Hawaii this summer for our anniversary. My question is this, what points should I collect over the next 10ish months so that we can fly and sleep in style (or at least cheap and fun) for Hawaii?

Details:
I've been collecting and using points since 2010. Between the two of us we have about 260,000 airline points in various programs (mainly AA and Continental). We don't really travel enough (2 trips this year) to do crazy things like mileage runs or gain any sort of status. We simply churn credit cards.

Our main airport is MKE,

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10ish months? For traveling in the summer using points you will need to book months in advance for desirable flights and hotels. All of the above suggestions are great! The DFW/HNL/OGG flights in First are nice. Also, the United 777 from Chicago in First. I prefer the AA seats over the United seats. Good Luck!

10ish months? For traveling in the summer using points you will need to book months in advance for desirable flights and hotels. All of the above suggestions are great! The DFW/HNL/OGG flights in First are nice. Also, the United 777 from Chicago in First. I prefer the AA seats over the United seats. Good Luck!

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+1 The meals on AA F is better than the ones on UA from what I've noticed as well.

Get an Alaska Airlines Visa, comes with a $99 companion ticket. Buy one Alaska Airlines ticket ORD-Seattle-Hawaii, even in first class, the second one is $99+tax. No capacity controls, any available seat, saves your miles and you don't worry about availability. Second ticket earns miles even.

Get an Alaska Airlines Visa, comes with a $99 companion ticket. Buy one Alaska Airlines ticket ORD-Seattle-Hawaii, even in first class, the second one is $99+tax. No capacity controls, any available seat, saves your miles and you don't worry about availability. Second ticket earns miles even.

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A great plan indeed, and while I have never implemented it myself, I have resommended it to friends who have been quite pleased with the results, especially the ability to book transcons from DCA.

The only minor issue for OP is that he will have to go to ORD, as MKE has no AS service.

Indeed, I did this with msgleff DCA-SEA-OGG and v.v. ... granted two 5 hour flights in each direction in an AS 737 ain't exactly the most comfortable way to fly even in F, but hard to beat the value when it was less than the cost of 2 coach tickets, I didn't spend any miles or upgrade certificates, and I had refundable/changable tickets which earned class of service bonuses and my first choice of flights.

Get an Alaska Airlines Visa, comes with a $99 companion ticket. Buy one Alaska Airlines ticket ORD-Seattle-Hawaii, even in first class, the second one is $99+tax. No capacity controls, any available seat, saves your miles and you don't worry about availability. Second ticket earns miles even.

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Gleff, I thought the companion ticket doesn't come until the anniversary of signing up for the card. Did I get that wrong?

Peteyboy,
A lot of good suggestions. I would reinforce the Starwood and Hyatt recommendations. Do you have your heart set upon traveling to a particular island? Do you currently have status with any hotel group?

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